A new synthetic route to allylsilanes: The reaction of silyllithium reagents with aromatic carbonyl compounds and aluminium tris(2,6-diphenylphenoxide) (ATPH)

Chemical Communications

Volumn , Issue 14, 1997, Pages 1299-1300

  Saito, Susumu ^a   Shimada, Kazuto ^a   Yamamoto, Hisashi ^a   Martínez De Marigorta, Eduardo ^b   Fleming, Ian ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b Department of Chemistry ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002541245     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702684f     Document Type: Article

References (34)

1. E. W. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, ch. 9; W. P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, 1983, ch. 11; I. Fleming, J. Dunoguès and R. Smithers, Org. React. (N.Y.), 1989, 37, 57.
2. E. W. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, ch. 9; W. P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, 1983, ch. 11; I. Fleming, J. Dunoguès and R. Smithers, Org. React. (N.Y.), 1989, 37, 57.
3. E. W. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, ch. 9; W. P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, 1983, ch. 11; I. Fleming, J. Dunoguès and R. Smithers, Org. React. (N.Y.), 1989, 37, 57.
4. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
5. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
6. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
7. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
8. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
9. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
10. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
11. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
12. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
13. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
14. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
15. T. K. Sarkar, Synthesis, 1990, 969 and 1101; I. Fleming, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 2, ed. C. H. Heathcock, ch. 2.2, pp. 563-593. Allylsilanes derived by silylation of allyl-metal species: M. C. Henry and J. G. Nortes, J. Am. Chem. Soc., 1960, 82, 555; V. F. Mironov and V. V. Nepomnina, Izv. Akad. Nauk SSSR, Ser. Khim., 1960, 1419 (Chem. Abstr., 1961, 55, 358); J.-P. Pillot, J. Dunoguès and R. Calas, Tetrahedron Lett., 1976, 1871. Allylsilanes derived from silylmethyl anions; K. Ito, M. Fukui and Y. Kurachi, J. Chem. Soc., Chem. Commun., 1977, 500; D. Seyferth, K. R. Wursthorn and R. E. Mammarella, J. Org. Chem., 1977, 42, 3104. Allylsilanes derived by nucleophilic allylic substitutions with silyl anions: I. Fleming and D. Marchi, Synthesis, 1981, 560; I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. I, 1992, 3331; J. G. Smith, S. E. Drozda, S. P. Petraglia, N. R. Quinn, E. M. Rice, B. S. Taylor and M. Viswanathan, J. Org. Chem., 1984, 49, 4112. Allylsilanes from β-silylcarbonyl compounds: I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. I, 1992, 3351.
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